Convenient synthesis and biological activities of pyridine derivatives of 3,4-dihydropyrimidin-2(1H)-ones

Article abstract of DOI:10.1002/jhet.390

2-Chloro-5-(chloromethyl)-pyridine reacted with 3,4-dihydropyrimidin-2(1H)- ones 1 to afford 1-[6-aryl-1-(6-chloropyridin-3-yl-methyl)-2-(6-chloropyridin-3- yl-methylthio)-4-methyl-1,6-dihydropyrimidin-5-yl] carboxylates or ethanones 2 in good yields. The

Full text of DOI:10.1002/jhet.390

572
Convenient Synthesis and Biological Activities of Pyridine
Derivatives of 3,4-Dihydropyrimidin-2(1H)-ones
Vol 48
Xiao-Fei Zhu and De-Qing Shi*
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry,
Central China Normal University, Wuhan 430079, Hubei, People’s Republic of China
*E-mail: chshidq@mail.ccnu.edu.cn
Received April 18, 2009
DOI 10.1002/jhet.390
Published online 4 March 2011 in Wiley Online Library (wileyonlinelibrary.com).
2-Chloro-5-(chloromethyl)-pyridine reacted with 3,4-dihydropyrimidin-2(1H)-ones 1 to afford 1-[6-
aryl-1-(6-chloropyridin-3-yl-methyl)-2-(6-chloropyridin-3-yl-methylthio)-4-methyl-1,6-dihydropyrimidin-
5-yl] carboxylates or ethanones 2 in good yields. The structure of the target compounds 2 was con-
1
firmed by IR, H NMR, EI-MS, and elemental analyses, and compound 2a was further characterized by
single crystal X-ray diffraction. The preliminary bioassay indicated that some of the title compounds
possess moderate insecticidal and fungicidal activities.
J. Heterocyclic Chem., 48, 572 (2011).
we designed and synthesized a series of 1-[6-aryl-1-(6-
chloropyridin-3-yl-methyl)-2-(6-chloropyridin-3-yl-meth-
ylthio)-4-methyl-1,6-dihydropyrimidin-5-yl]carboxylates
or ethanones 2, which have both the skeletons of
DMHP and pyridine moieties.
INTRODUCTION
The latest class of chemical insecticides with out-
standing economically impact on the agrochemical
industry comprises the neonicotinoid insecticides, which
act agonistically and show high selectivity to insect nic-
otinic acetylcholine receptor. A lot of new insecticides,
such as imidacloprid, acetamiprid, and nitenpyram have
been commercialized (Scheme 1) and widely used as
neonicotinoid insecticides with relatively low human
toxicity [1,2]. It was found that most of the biologically
active neonicotinic compounds contain the aminome-
thylpyridine moiety [3,4]. Moreover, many compounds
containing pyridyl are also known to possess a wide
range of biological and pharmacological activities, as
well as low toxicity toward mammals [5–8]. Recently,
3,4-dihydropyrimidin-2(1H)-ones (DHPMs) and their
derivatives have attracted considerable interest because
of their significant therapeutic and pharmacological
properties, such as antiviral, antitumor, antibacterial, and
antihypertensive effects [9–11]. There are some reports
on the S-alkylation of DHPMs, and the alkylation
reagents are usually benzyl and allyl halides [12,13].
However, there are few reports on the N, S-dialkylation
of DHPMs in one pot reaction. As a continuation of our
search for new biologically active compounds [14,15],
RESULTS AND DISCUSSION
DHPMs reacted with 2-chloro-5-(chloromethyl)-pyri-
dine to afford the target products 2 in high yields and
no mono S-alkylation product was detected even with
excess (3ꢀ4 equimolecular) DHPMs. It was found that
the bases played a major role in the alkylation reaction,
when triethyl amine was used, the yield of product 2
was very low (about 20%) under refluxing for 12 h;
however, when anhydrous potassium carbonate was
used, the reaction underwent very smoothly at room
temperature and the yields were also good (Scheme 2).
All products were fully characterized by IR, 1H
NMR, mass spectra, and elemental analysis. All the
spectral data were in accordance with the anticipated
1
structures. In the H NMR spectra of 2, both of the two
protons of CH2N and CH2S moieties displayed as two
doublets, giving the chemical shifts d in 4.3, 4.4 and
4.2, 4.7, respectively. The 6-position proton of 1,6-
C
V
2011 HeteroCorporation

May 2011
Convenient Synthesis and Biological Activities of Pyridine Derivatives of
3,4-Dihydropyrimidin-2(1H)-ones
573
Scheme 1
dihydropyrimidine exhibited as a singlet with chemical
shift d between 5.0 and 5.5. IR spectra of compounds 2
showed normal stretching absorption bands, indicating
the existence of C¼¼O (ꢀ1668 cmꢁ1), C¼¼N (ꢀ1560
cmꢁ1). The EI mass spectra of compounds 2 revealed
the existence of the molecular ion peaks and anticipant
fragmentation peaks (e.g., compound 2b, molecular ion
peak: 510), which were in good accordance with the
given structures of products.
the title compounds possess moderate insecticidal activ-
ity, for example, compound 2h exhibited 71.4% death
rate against aphides at this dosage.
The fungicidal activities of the target compounds 2
were tested at a concentration of 50 mg/L. The six fungi
used, Fusarium oxysporium, Rhizoctonia solani, Botrytis
cinereapers, Gibberella zeae, Dothiorella gregaria, and
Colletotrichum gossypii, belongs to the group of field
fungi and were isolated from corresponding crops. The
activity data were also listed in Table 2. The prelimi-
nary bioassay indicated that the title compounds 2 pos-
sess moderate to weak inhibitory activities against the
above six fungi, for example, compound 2f showed 78,
64, and 69% inhibitory activities against Rhizoctonia
solani, Gibberella zeae, and Dothiorella gregaria fungi,
respectively. Further structure-activity relationships are
under investigation.
Moreover, to confirm their molecular structure abso-
lutely, a single crystal of 2a was obtained as colorless
crystals from a dichloromethane and hexane (1:3 v/v).
X-ray diffraction analysis indicates that the single crys-
tal of 2a is triclinic with space group P-1, cell parame-
˚
ters a ¼ 10.289 (1), b ¼ 11.149 (1), c ¼ 12.639 (1) A,
a ¼ 104.740 (2), b ¼ 95.725 (2), c ¼ 116.332 (2)ꢂ, v ¼
3
3
˚
1218.1 (2) A , z ¼ 2, Dc ¼ 1.450 g/cm , F (000) ¼
548, l ¼ 0.489 mmꢁ1, and final R ¼ 0.0502, wR ¼
0.1236 for 5262 reflections (I > r(I)). Figures 1 and 2
shows the molecular structure of compound 2a
and packing of the molecules in the unit cell, respec-
tively. Intermolecular C(5)AH(5)ꢃꢃꢃO1i and C(25)AH
(25)ꢃꢃꢃ(O1)i [symmetry code: (i) –x, ꢁy, ꢁz] hydrogen
bonds link two molecules together, these pairs are linked
In conclusion, a series of 1-[6-aryl-1-(6-chloropyridin-
3-yl-methyl)-2-(6-chloropyridin-3-yl-methylthio)-4-methyl-
1,6-dihydropyrimidin-5-yl] carboxylates or ethanones 2
were synthesized via the alkylation reaction of DHPMs
with 2-chloro-5-(chloromethyl)-pyridine. The results of
the preliminary bioassays indicated that some of the title
compounds possess moderate fungicidal and insecticidal
activity.
into
a
three-dimensional network by C(17)A
H(17)ꢃꢃꢃCl(3)ii [symmetry code: (ii) –xþ1, ꢁy, ꢁz] inter-
actions (Fig. 2 and Table 1).
EXPERIMENTAL
Compounds 2 were tested for insecticidal activity
against aphides at the concentration of 250 mg/L
according to a previously reported method [16]. The
result is listed in Table 2, which indicated that some of
Melting points were determined with a WRS-1B digital
1
melting point apparatus and are uncorrected. H NMR spectra
were recorded with a Varian Mercury PLUS400 (400 MHz)
Scheme 2
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

574
X.-F. Zhu and D.-Q. Shi
Vol 48
Table 1
Hydrogen-bond geometry (A, ꢂ).
˚
D-HꢃꢃꢃA
D-H
HꢃꢃꢃA
DꢃꢃꢃA
D-HꢃꢃꢃA
C(5)AH(5)ꢃꢃꢃO(1)i
0.93
0.93
0.93
2.42
2.55
2.80
3.326 (3)
3.348 (3)
3.564 (3)
165
144
140
C(25)AH(25)ꢃꢃꢃO(1)i
C(17)AH(17)ꢃꢃꢃCl(3)ii
Symmetry codes: (i) ꢁx, ꢁy, ꢁz; (ii) ꢁxþ1, ꢁy, ꢁz
raphy on silica gel using ethyl acetate/petroleum ether (3:4, V/
V) as the eluent to give 2a–2i as yellow crystals or yellow oil.
1-[6-(4-chlorophenyl)-1-(6-chloropyridin-3-yl-methyl)-2-(6-
chloropyridin-3-yl-methylthio)-4-methyl-1,6-dihydropyrimidin-
5-yl]ethanone (2a). Yellow crystals, yield: 88%, mp 104–
106ꢂC; IR: 3055 (ArH), 1619 (C¼¼O), 1584, 1566 (C¼¼N),
Figure 1. The structure of 2a, showing displacement ellipsoids at the
50% probability level for non-H atoms. [Color figure can be viewed in
the online issue, which is available at wileyonlinelibrary.com.]
1
1488, 1460 cmꢁ1; H NMR: d 2.28 (s, 3H, CH3), 2.42 (s, 3H,
CH3), 4.21 (d, J ¼ 16 Hz, 1H, SCH2), 4.30 (d, J ¼ 14.4 Hz,
1H, NCH2), 4.42 (d, J ¼ 14.0 Hz, 1H, NCH2), 4.73 (d, J ¼
16.4 Hz, 1H, SCH2), 5.30 (s, 1H, CHAr), 7.12–7.32 (m, 4H,
ArH), 7.41 (d, J ¼ 7.6 Hz, 2H, PyH), 7.67 (d, J ¼ 7. 6 Hz,
2H, PyH), 8.22 (s, 1H, PyH), 8.45 (s, 1H, PyH); ms (70 eV):
m/z 530 (Mþ, 56.0), 418 (94.2), 263 (100), 246 (31.9), 158
(29.4), 135 (96.4), 87 (99.6), 71 (99.3), 57 (93.5), 48 (97.2).
Anal. Calcd. for C25H21Cl3N4OS: C, 56.45; H, 3.98; N, 10.53.
Found: C, 56.64; H, 4.18; N, 10.39.
spectrometer with TMS as the internal reference and CDCl3 as
the solvent, while mass spectra were obtained with a Finnigan
TRACEMS2000 spectrometer using the EI method. IR spectra
were measured by a Nicolet NEXUS470 spectrometer. Ele-
mental analyses were performed with an Elementar Vario
ELIIICHNSO elemental analyzer. X-ray diffraction analysis
was performed on a Bruker SMART 1000 CCD diffractometer.
DHPMs were synthesized according to the reported method
[17], all of the solvents and materials were reagent grade and
purified as required.
Preparation of 1-[1-(6-chloropyridin-3-yl-methyl)-2-(6-
chloropyridin-3-yl-methylthio)-4-methyl-6-aryl-1,6-dihydro-
pyrimidin-5-yl]carboxylate or ethanone 2: General
procedure. The mixture of DHPM 1 (2 mmol), 2-chloro-5-
(chloromethyl)-pyridine (0.65 g, 4 mmol), K2CO3 (0.55 g, 5
mmol), and anhydrous CH3CN (25 mL) was stirred at room
temperature until the reaction was complete (monitored by
TLC). After the solid was filtered off, the filtrate was concen-
trated and the residue was purified by flash column chromatog-
1-[1-(6-chloropyridin-3-yl-methyl)-2-(6-chloropyridin-3-yl-
methylthio)-4-methyl-6-(4-tolyl)-1,6-dihydropyrimidin-5-yl]e-
thanone (2b). Yellow crystals, yield: 85%, mp 125–127ꢂC;
IR: 3047(ArH), 1621(C¼¼O), 1586, 1565(C¼¼N), 1491, 1459
1
cmꢁ1; H NMR: d 2.24 (s, 3H, CH3), 2.31 (s, 3H, CH3), 2.40
(s, 3H, CH3), 4.22 (d, J ¼ 14.4 Hz, 1H, SCH2), 4.31(d, J ¼
10.8 Hz, 1H, NCH2), 4.43 (d, J ¼ 10.8 Hz, 1H, NCH2), 4.70
(d, J ¼ 12 Hz, 1H, SCH2), 5.25 (s, H, CHAr), 7.08–7.31 (m,
4H, ArH), 7.42 (s, 2H, PyH), 7.67 (d, J ¼ 6.8 Hz, 2H, PyH),
8.22 (s, 1H, PyH), 8.44 (s, 1H, PyH); ms (70 eV): m/z 510
(Mþ, 84.2), 417 (91.4), 350 (99.8), 260 (60.3), 228 (17.6), 136
(73.3), 113 (92.2), 87 (100), 71 (98.4), 57 (95.1), 48 (98.1).
Anal. Calcd. for C26H24Cl2N4OS: C, 61.06; H, 4.73; N, 10.95.
Found: C, 61.20; H, 4.60; N, 10.87.
1-[1-(6-chloropyridin-3-yl-methyl)-2-(6-chloropyridin-3-yl-me-
thylthio)-4-methyl-6-phenyl-1,6-dihydropyrimidin-5-yl]ethanone
(2c). Yellow oil, yield: 90%; 1H NMR: d 2.23 (s, 3H, CH3),
2.41(s, 3H, CH3), 4.23 (d, J ¼ 12.4 Hz, 1H, SCH2), 4.35 (d, J
¼ 10.4 Hz, 1H, NCH2), 4.44 (d, J ¼ 10.8 Hz, 1H, 1NCH2),
4.71 (d, J ¼ 12.4 Hz, 1H, SCH2), 5.31 (s, H, CHAr), 7.18–
7.31 (m, 5H, ArH), 7.42 (d, J ¼ 7.6 Hz, 2H, PyH), 7.67 (d, J
¼ 8.4 Hz, 2H, PyH), 8.23 (s, 1H, PyH), 8.45 (s, 1H, PyH); ms
(70 eV): m/z 485 (Mþ, 5.0), 232 (40.2), 132 (80.6), 77 (100),
63 (30.3). Anal. Calcd. for C25H22Cl2N4OS: C, 60.36; H, 4.46;
N, 11.26. Found: C, 60.49; H, 4.51; N, 11.39.
1-[1-(6-chloropyridin-3-yl-methyl)-2-(6-chloropyridin-3-yl-
methylthio)-6-(4-methoxyphenyl)-4-methyl-1,6-dihydropyrimi-
din-5-yl]ethanone (2d). Yellow crystals, yield: 92%, mp 97–
99ꢂC; IR: 3050 (ArH), 1622 (C¼¼O), 1584, 1566 (C¼¼N),
1
1488, 1460 cmꢁ1; H NMR: d 2.24 (s, 3H, CH3), 2.41 (s, 3H,
CH3), 3.78 (s, 3H, CH3), 4.29 (d, J ¼ 12.4 Hz, 1H, SCH2),
4.31 (d, J ¼ 11.4 Hz, 1H, NCH2), 4.43 (d, J ¼ 10.8 Hz, 1H,
NCH2), 4.71 (d, J ¼ 12 Hz, 1H, SCH2), 5.22 (s, 1H, CHAr),
6.78–7.31 (m, 4H, ArH), 7.42 (s, 2H, PyH), 7.70 (s, 2H, PyH),
8.23 (s, 1H, PyH), 8.45 (s, 1H, PyH). Anal. Calcd. for
Figure 2. Part of the crystal packing of 2a, showing molecules linked
into pairs by C---HꢃꢃꢃO interactions (dashed lines). The pairs are linked
further by C---HꢃꢃꢃCl interactions (dashed lines). H atoms not involved
in these interactions have been omitted. [Color figure can be viewed in
the online issue, which is available at wileyonlinelibrary.com.]
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

May 2011
Convenient Synthesis and Biological Activities of Pyridine Derivatives of
3,4-Dihydropyrimidin-2(1H)-ones
575
Table 2
The insecticidal and fungicidal activities of compounds of 2a–2i (inhibitory rate %).
Insecticidal activity (250 mg/L)
Fungicidal activity (50 mg/L)
Fusarium
oxysporium
Rhizoctonia
solani
Botrytis
cinereapers
Gibberella
zeae
Dothiorella
gregaria
Colletotrichum
gossypii
Compd.
Aphides
2a
2b
2c
2d
2e
2f
2g
2h
2i
20.5
52.0
18.4
28.5
6.7
40.6
36.0
71.4
65.8
13
39
29
26
32
26
14
35
45
19
44
64
31
38
78
34
38
56
27
41
29
12
26
44
12
26
32
12
24
18
42
58
64
17
35
48
14
16
28
39
12
69
32
11
38
14
37
53
15
26
26
48
26
54
C26H24Cl2N4O2S: C, 59.20; H, 4.59; N, 10.62. Found: C,
59.36; H, 4.63; N, 10.61.
CH3), 3.96–4.02 (m, 2H, OCH2), 4.09 (d, J ¼ 14 Hz, 1H,
SCH2), 4.27 (d, J ¼ 10.4 Hz, 1H, NCH2), 4.44 (d, J ¼ 10.8
Hz, 1H, NCH2), 4.70 (d, J ¼ 14.4 Hz, 1H, SCH2), 5.12 (s, 1H,
CHAr), 7.19–7.28 (m, 7H, ArH, PyH), 7.44 (d, J ¼ 10 Hz,
1H, PyH), 7.69 (d, J ¼ 8 Hz, 1H, PyH), 8.23 (s, 1H, PyH),
8.44 (s, 1H, PyH); ms (70 eV): m/z 526 (Mþ, 12.6), 448(15.3),
323 (11.3), 273 (11.6), 158 (8.3), 125 (100), 89 (20.5), 77
(14.6), 63 (20.0). Anal. Calcd. for C26H24Cl2N4O2S: C, 59.20;
H, 4.59; N, 10.62. Found: C, 59.32; H, 4.47; N, 10.71.
1-[1-(6-chloropyridin-3-yl-methyl)-2-(6-chloropyridin-3-yl-
methylthio)-4-methyl-6-(thiophen-2-yl)-1,6-dihydropyrimidin-5-
yl]ethanone (2e). Yellow oil, yield: 77%; IR: 3050 (ArH),
1
1625 (C¼¼O), 1580, 1570 (C¼¼N), 1505, 1464 cmꢁ1; H NMR:
d 2.29 (s, 3H, CH3), 2.41(s, 3H, CH3), 4.37(d, J ¼ 12.8 Hz,
1H, SCH2), 4.38 (d, J ¼ 10.8 Hz, 1H, NCH2), 4.43 (d, J ¼
10.4 Hz, 1H, NCH2), 4.79 (d, J ¼ 12 Hz, 1H, SCH2), 5.30 (s,
H, CHAr), 5.60–5.66 (m, 1H, Thiophene-H), 6.83 (d, J ¼ 15
Hz, 2H, Thiophene-H), 7.17 (d, J ¼ 4.8 Hz, 1H, PyH), 7.28
(d, J ¼ 6.0 Hz, 1H, PyH), 7.44 (d, J ¼ 8.0 Hz, 1H, PyH),
7.67 (d, J ¼ 6.4 Hz, 1H, PyH), 8.25 (s, 1H, PyH), 8.42 (s, 1H,
PyH). Anal. Calcd. for C23H20Cl2N4OS2: C, 54.87; H, 4.00, N,
11.13. Found: C, 54.78; H, 4.12; N, 11.07.
Ethyl 1-[1-(6-chloropyridin-3-yl-methyl)-2-(6-chloropyridin-
3-yl-methylthio)-6-(4-methoxyphenyl)-4-methyl-1,6-dihydropyri-
midin-5-yl]carboxylate (2i). Yellow crystals, yield 93%, mp
1
112–114ꢂC; H NMR: d 1.14 (t, J ¼ 7.6 Hz, 3H, CH3), 2.40
(s, 3H, CH3), 3.77 (s, 3H, CH3), 3.96–4.02 (m, 2H, OCH2),
4.09 (d, J ¼ 16 Hz, 1H, SCH2), 4.30 (d, J ¼ 10.4 Hz, 1H,
NCH2), 4.41 (d, J ¼ 10.8 Hz, 1H, NCH2), 4.67 (d, J ¼ 16.4
Hz, 1H, SCH2), 5.05 (s, H, CHAr), 6.79–7.30 (m, 6H, ArH,
PyH), 7.44 (d, J ¼ 8 Hz, 1H, PyH), 7.68 (d, J ¼ 6.8 Hz, 1H,
PyH), 8.23 (s, 1H, PyH), 8.44 (s, 1H, PyH); ms (70 eV): m/z
556 (Mþ, 100), 526 (11.4), 511 (24.6), 483 (43.9). Anal.
Calcd. for C27H26Cl2N4O3S: C, 58.17; H, 4.70; N, 10.05.
Found: C, 58.14; H, 4.57; N, 10.19.
1-[1-(6-chloropyridin-3-yl-methyl)-2-(6-chloropyridin-3-yl-me-
thylthio)-4-methyl-6-(4-nitrophenyl)-1,6-dihydropyrimidin-5-yl]e-
thanone (2f). Yellow crystals, yield 65%, mp 171–173ꢂC; 1H
NMR: d 2.34 (s, 3H, CH3), 2.44 (s, 3H, CH3), 4.21 (d, J ¼
15.6 Hz, 1H, SCH2), 4.35 (d, J ¼ 10.8 Hz, 1H, NCH2), 4.58
(d, J ¼ 11.4 Hz, 1H, NCH2), 4.79 (d, J ¼ 16 Hz, 1H, SCH2),
5.50 (s, H, CHAr), 7.26–7.38 (m, 4H, ArH), 7.41 (d, J ¼ 8.0
Hz, 2H, PyH), 7.69 (d, J ¼ 8.0 Hz, 2H, PyH), 8.22 (s, 1H,
PyH), 8.47 (s, 1H, PyH). Anal. Calcd. for C25H21Cl2N5O3S: C,
55.36; H, 3.90; N, 12.91. Found: C, 55.18; H, 3.82; N, 12.77.
Ethyl 1-[1-(6-chloropyridin-3-yl-methyl)-2-(6-chloropyridin-
3-yl-methylthio)-4-methyl-6-(4-tolyl)-1,6-dihydropyrimidin-5-
yl]carboxylate (2g.) Yellow crystals, yield 89%, mp 128–
129ꢂC; IR: 3053 (ArH), 1660 (C¼¼O), 1599, 1586, 1564
FUNGICIDAL ACTIVITY TESTING
The fungicidal activity measurement method was
adapted from the one described by Molina et al. [18].
The synthesized target compounds were dissolved in
0.5–1.0 mL of DMF and diluted with distilled water to
the concentration of 500 mg/L. The solutions (1 mL)
were mixed rapidly with thawed potato glucose agar
culture medium (9 mL) under 50ꢂC. The mixtures were
poured into Petri dishes. After the dished were cooled,
the solidified plates were incubated with 4 mm myce-
lium disk, inverted, and incubated at 28ꢂC for 48 h. Dis-
tilled water was used as the blank control. Three repli-
cates of each test were carried out. The mycelial elonga-
tion radius (mm) of fungi settlements was measured af-
ter 48 h of culture. The growth inhibitory rates were cal-
culated with the following equation: I ¼ [(CꢁT)/C] ꢄ
(C¼¼N), 1501, 1460 cmꢁ1
;
1H NMR: d 1.14 (t, J ¼ 7.6 Hz,
3H, CH3), 2.32 (s, 3H, CH3), 2.39 (s, 3H, CH3), 3.96–4.01 (m,
2H, OCH2), 4.20 (d, J ¼ 16.4 Hz, 1H, SCH2), 4.30 (d, J ¼
10.0 Hz, 1H, NCH2), 4.41 (d, J ¼ 10.4 Hz, 1H, NCH2), 4.68
(d, J ¼ 16.0 Hz, 1H, SCH2), 5.07(s, H, CHAr), 7.06–7.11 (m,
4H, ArH), 7.27 (d, J ¼ 10.4 Hz, 2H, PyH), 7.45 (d, J ¼ 7.2
Hz, 1H, PyH), 7.68 (d, J ¼ 8 Hz, 1H, PyH), 8.22 (s, 1H,
PyH), 8.44 (s, 1H, PyH). Anal. Calcd. for C27H26Cl2N4O2S: C,
59.89; H, 4.84; N, 10.35. Found: C, 60.02; H, 4.89; N, 10.30.
Ethyl 1-[1-(6-chloropyridin-3-yl-methyl)-2-(6-chloropyridin-
3-yl-methylthio)-4-methyl-6-phenyl-1,6-dihydropyrimidin-5-yl]
carboxylate (2h). Yellow crystals, yield 91%, mp 68–70ꢂC;
IR: 3054 (ArH), 1668 (C¼¼O), 1606, 1564 (C¼¼N), 1504, 1459
1
cmꢁ1; H NMR: d 1.14 (t, J ¼ 8.0 Hz, 3H, CH3), 2.41 (s, 3H,
Journal of Heterocyclic Chemistry
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X.-F. Zhu and D.-Q. Shi
Vol 48
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the Natural Science Foundation of Hubei Province (Grant
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet